Bourbon & Cigars: Tips For Pairing Two Luxurious Worlds

Since 2002, Windy City Cigars has been offering the convenience of buying cigars online directly through our site to our customers. We’ve now become the biggest online cigar retailer and we’re very proud of that. On our site, you’ll find the best prices, best selection, and always in stock favorites and accessories. A lot of customers come into our store or call us and ask us to recommend cigar pairings for Bourbon. We’ve got some suggestions for you!

People spend years looking for the perfect bourbon and cigar combination. We suggest matching cigars and bourbons that have similar body strengths.

Four Roses Bourbon: This is one of the lightest bourbons with honey, anise, walnut, and caramel notes. This pairs well with light-bodied cigars like the Macanudo Prince Phillip

Evan William’s Single Barrel: This is a light-to-medium bodied bourbon that mixes oranges, vanilla, and anise flavors with a sweet caramel nose and a long finish. This pairs well with Macanudo Prince Phillip cigars as it draws out the creamy, spicy sweetness. It pairs even better with Padrón 1964 Anniversary Series Exclusivo.

Booker’s: This orange, vanilla, leather, pecan, honey, and cherry bourbon could be called a high-octane bourbon. The 125 proof bourbon pairs well with the Montecristo #2 cigars as it pulls flavors from the cigar that aren’t apparent before. 

Pappy Van Winkle’s Family Reserve: This hard to find, full-bodied bourbon gives woody, smoky, almond, and cherry tastes that are alluring to some but considered an acquired taste. It matches well with the Montecristo #2 where it finds cocoa and cedar qualities that are downplayed in the cigar. The Arturo Fuente Opus X cigars also pair quite well.

Which Cigars are Better: Bigger or Smaller